# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2014sot0046
_database_code_depnum_ccdc_archive 'CCDC 1060573'
_audit_update_record             
;
2015-04-20 deposited with the CCDC.
2015-10-30 downloaded from the CCDC.
;
_audit_creation_date             2014-10-07
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2014.10.02 svn.r3027 for OlexSys, GUI svn.r4900)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H11 N3 O6'
_chemical_formula_sum            'C17 H11 N3 O6'
_chemical_formula_weight         353.29
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.9877(5)
_cell_length_b                   15.1541(7)
_cell_length_c                   10.2131(6)
_cell_angle_alpha                90
_cell_angle_beta                 103.161(5)
_cell_angle_gamma                90
_cell_volume                     1505.20(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6234
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.7430
_cell_measurement_theta_min      2.1410
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       fragment
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0709
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14536
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.699
_diffrn_reflns_theta_min         3.380
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -40.00   68.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.0000   72.0000  120.0000 108

#__ type_ start__ end____ width___ exp.time_
  2 omega  -72.00   17.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.0000  -72.0000    0.0000 89

#__ type_ start__ end____ width___ exp.time_
  3 omega  -78.00   17.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.0000  -72.0000 -180.0000 95

#__ type_ start__ end____ width___ exp.time_
  4 omega  -67.00   15.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.0000    0.0000  -30.0000 82

#__ type_ start__ end____ width___ exp.time_
  5 omega  -37.00  -10.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.0000   54.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
  6 omega  -61.00  -51.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.0000   72.0000 -180.0000 10

#__ type_ start__ end____ width___ exp.time_
  7 omega  -97.00  -73.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.0000  -72.0000 -120.0000 24
;
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 FRE-HF'
_diffrn_measurement_device_type2 'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_UB_11      -0.0502560000
_diffrn_orient_matrix_UB_12      0.0046371000
_diffrn_orient_matrix_UB_13      -0.0611338000
_diffrn_orient_matrix_UB_21      -0.0500267000
_diffrn_orient_matrix_UB_22      -0.0189953000
_diffrn_orient_matrix_UB_23      0.0306127000
_diffrn_orient_matrix_UB_31      -0.0169773000
_diffrn_orient_matrix_UB_32      0.0425327000
_diffrn_orient_matrix_UB_33      0.0204465000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           45.0
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3045
_reflns_number_total             3884
_reflns_odcompleteness_completeness 93.21
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     32.00
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
'CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05)'
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_refine_diff_density_max         1.092
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.113
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3884
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1725
_refine_ls_R_factor_gt           0.1503
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0833P)²+11.7598P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3307
_refine_ls_wR_factor_ref         0.3428
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C11(H11), C13(H13), C14(H14), C16(H16), C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7961(6) 0.7628(3) 0.5898(5) 0.0518(13) Uani 1 1 d . . . . .
O2 O 0.7936(5) 0.6736(3) 0.7522(5) 0.0455(11) Uani 1 1 d . . . . .
O3 O 0.8271(4) 0.3736(2) 0.5347(5) 0.0426(11) Uani 1 1 d . . . . .
O4 O 0.9734(5) 0.0749(3) 0.3779(5) 0.0487(12) Uani 1 1 d . . . . .
O5 O 0.4651(5) -0.1386(4) 0.1269(6) 0.0607(15) Uani 1 1 d . . . . .
O6 O 0.4820(5) -0.1878(3) 0.3297(6) 0.0575(14) Uani 1 1 d . . . . .
N1 N 0.7980(5) 0.6882(3) 0.6360(5) 0.0336(10) Uani 1 1 d . . . . .
N2 N 0.8342(6) 0.3960(3) 0.3142(6) 0.0423(12) Uani 1 1 d . . . . .
N3 N 0.4973(5) -0.1309(4) 0.2500(7) 0.0453(14) Uani 1 1 d . . . . .
C1 C 0.8082(5) 0.6129(3) 0.5509(6) 0.0311(12) Uani 1 1 d . . . . .
C2 C 0.8111(6) 0.6303(4) 0.4168(6) 0.0338(12) Uani 1 1 d . . . . .
H2 H 0.8052 0.6894 0.3849 0.041 Uiso 1 1 calc R . . . .
C3 C 0.8225(7) 0.5621(4) 0.3310(7) 0.0408(14) Uani 1 1 d . . . . .
H3 H 0.8275 0.5731 0.2406 0.049 Uiso 1 1 calc R . . . .
C4 C 0.8264(6) 0.4773(4) 0.3806(7) 0.0365(13) Uani 1 1 d . . . . .
C5 C 0.8226(5) 0.4633(3) 0.5127(6) 0.0337(13) Uani 1 1 d . . . . .
C6 C 0.8151(6) 0.5294(3) 0.6058(6) 0.0329(12) Uani 1 1 d . . . . .
H6 H 0.8149 0.5181 0.6972 0.039 Uiso 1 1 calc R . . . .
C7 C 0.8337(6) 0.3411(4) 0.4077(7) 0.0383(14) Uani 1 1 d . . . . .
C8 C 0.8361(6) 0.2439(4) 0.3952(7) 0.0388(14) Uani 1 1 d . . . . .
H8 H 0.8407 0.2211 0.3045 0.047 Uiso 1 1 calc R . . . .
C9 C 0.7554(6) 0.1894(4) 0.4699(6) 0.0359(12) Uani 1 1 d . . . . .
H9 H 0.7068 0.2226 0.5299 0.043 Uiso 1 1 calc R . . . .
C10 C 0.9117(6) 0.1907(4) 0.5117(6) 0.0370(13) Uani 1 1 d . . . . .
H10 H 0.9534 0.2239 0.5956 0.044 Uiso 1 1 calc R . . . .
C11 C 0.9907(6) 0.1134(4) 0.4797(7) 0.0399(14) Uani 1 1 d . . . . .
H11 H 1.0635 0.0929 0.5500 0.048 Uiso 1 1 calc R . . . .
C12 C 0.6827(6) 0.1074(4) 0.4045(7) 0.0406(14) Uani 1 1 d . . . . .
C13 C 0.6933(6) 0.0337(4) 0.4837(7) 0.0374(13) Uani 1 1 d . . . . .
H13 H 0.7440 0.0362 0.5744 0.045 Uiso 1 1 calc R . . . .
C14 C 0.6311(6) -0.0441(4) 0.4329(6) 0.0312(11) Uani 1 1 d . . . . .
H14 H 0.6408 -0.0953 0.4878 0.037 Uiso 1 1 calc R . . . .
C15 C 0.5560(5) -0.0473(4) 0.3043(6) 0.0324(12) Uani 1 1 d . . . . .
C16 C 0.5392(6) 0.0266(5) 0.2219(7) 0.0431(15) Uani 1 1 d . . . . .
H16 H 0.4857 0.0240 0.1323 0.052 Uiso 1 1 calc R . . . .
C17 C 0.6029(7) 0.1045(4) 0.2743(8) 0.0488(17) Uani 1 1 d . . . . .
H17 H 0.5917 0.1563 0.2204 0.059 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.224(6) . ?
O2 N1 1.219(6) . ?
O3 C5 1.376(6) . ?
O3 C7 1.403(8) . ?
O4 C11 1.169(8) . ?
O5 N3 1.230(8) . ?
O6 N3 1.219(8) . ?
N1 C1 1.452(7) . ?
N2 C4 1.416(7) . ?
N2 C7 1.267(9) . ?
N3 C15 1.452(7) . ?
C1 C2 1.402(8) . ?
C1 C6 1.380(7) . ?
C2 H2 0.9500 . ?
C2 C3 1.376(8) . ?
C3 H3 0.9500 . ?
C3 C4 1.379(9) . ?
C4 C5 1.375(9) . ?
C5 C6 1.395(8) . ?
C6 H6 0.9500 . ?
C7 C8 1.480(8) . ?
C8 H8 1.0000 . ?
C8 C9 1.481(9) . ?
C8 C10 1.492(8) . ?
C9 H9 1.0000 . ?
C9 C10 1.522(8) . ?
C9 C12 1.515(8) . ?
C10 H10 1.0000 . ?
C10 C11 1.489(9) . ?
C11 H11 0.9500 . ?
C12 C13 1.369(9) . ?
C12 C17 1.387(10) . ?
C13 H13 0.9500 . ?
C13 C14 1.377(8) . ?
C14 H14 0.9500 . ?
C14 C15 1.357(8) . ?
C15 C16 1.388(8) . ?
C16 H16 0.9500 . ?
C16 C17 1.390(10) . ?
C17 H17 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O3 C7 101.6(5) . . ?
O1 N1 C1 119.5(5) . . ?
O2 N1 O1 122.9(5) . . ?
O2 N1 C1 117.6(5) . . ?
C7 N2 C4 101.5(5) . . ?
O5 N3 C15 117.5(6) . . ?
O6 N3 O5 124.9(6) . . ?
O6 N3 C15 117.6(6) . . ?
C2 C1 N1 117.2(5) . . ?
C6 C1 N1 118.8(5) . . ?
C6 C1 C2 124.0(5) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.2(5) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 121.1 . . ?
C2 C3 C4 117.8(6) . . ?
C4 C3 H3 121.1 . . ?
C3 C4 N2 129.4(6) . . ?
C5 C4 N2 110.6(5) . . ?
C5 C4 C3 120.0(5) . . ?
O3 C5 C6 127.0(6) . . ?
C4 C5 O3 107.8(5) . . ?
C4 C5 C6 125.2(5) . . ?
C1 C6 C5 112.8(5) . . ?
C1 C6 H6 123.6 . . ?
C5 C6 H6 123.6 . . ?
O3 C7 C8 115.7(6) . . ?
N2 C7 O3 118.4(5) . . ?
N2 C7 C8 125.9(6) . . ?
C7 C8 H8 115.4 . . ?
C7 C8 C9 119.3(6) . . ?
C7 C8 C10 119.0(5) . . ?
C9 C8 H8 115.4 . . ?
C9 C8 C10 61.6(4) . . ?
C10 C8 H8 115.4 . . ?
C8 C9 H9 115.6 . . ?
C8 C9 C10 59.6(4) . . ?
C8 C9 C12 119.5(5) . . ?
C10 C9 H9 115.6 . . ?
C12 C9 H9 115.6 . . ?
C12 C9 C10 119.4(5) . . ?
C8 C10 C9 58.8(4) . . ?
C8 C10 H10 116.5 . . ?
C9 C10 H10 116.5 . . ?
C11 C10 C8 116.6(6) . . ?
C11 C10 C9 119.3(5) . . ?
C11 C10 H10 116.5 . . ?
O4 C11 C10 127.5(6) . . ?
O4 C11 H11 116.3 . . ?
C10 C11 H11 116.3 . . ?
C13 C12 C9 116.3(6) . . ?
C13 C12 C17 119.4(6) . . ?
C17 C12 C9 124.2(6) . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.5(6) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.9(6) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 N3 119.2(5) . . ?
C14 C15 C16 121.4(5) . . ?
C16 C15 N3 119.3(6) . . ?
C15 C16 H16 121.0 . . ?
C15 C16 C17 118.1(6) . . ?
C17 C16 H16 121.0 . . ?
C12 C17 C16 120.6(6) . . ?
C12 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id mm-7AS-60
_olex2_submission_special_instructions 'No special instructions were received'
